Jewish prayer may be conceived as a self-reflective conversation between the supplicant and the Divine, an anchor in moments of challenge or success, and a tool for clarifying values, meaning and purpose. Acquisition of tefilla (prayer) skills is an important goal during adolescence, and psychological and biological changes occurring during adolescence accentuate the relevance of positive tefilla experiences. Appropriate engagement of middle school and high school students by the Yeshiva school community can play a significant role in the development of an adolescent’s Jewish identity and lifelong commitment to prayer. The purpose of this study was to explore factors critical to student engagement in tefilla during adolescence, particularly those that may create a foundation for lifelong tefilla practice.